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Results: 191 Rentals

  • Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
    From $366 per night (USD)

    VRBO

    Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    11

    Awesome lake house, with a private dock, kayaks, a canoe, a game room with foosball, air hockey/small pool table, an arc ...

    From $366 per night (USD)

    VRBO

    Details
  • Serenity Retreat, Confidently Clean
    From $110 per night (USD)

    Expedia

    Serenity Retreat, Confidently Clean

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This is a unique 2 story antique building that has been completely renovated and sectioned into 2 small apartments on t ...

    From $110 per night (USD)

    Expedia

    Details
  • Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
    From $394 per night (USD)

    VRBO

    Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Lake Silver Retreat III is a home with options ~ you can rent it as a 3 bedroom or a 5 bedroom (some holidays exclusions ...

    From $394 per night (USD)

    VRBO

    Details
  • *Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
    From $99 per night (USD)

    Expedia

    *Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    WELCOME! Lake Mariam Tiny Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, our spa ...

    From $99 per night (USD)

    Expedia

    Details
  • Lake Idylwild Delight: Waterfront Lakehouse, Private Dock, Tiki Bar, Kid's Jungle Gym, Near Legoland
    From $350 per night (USD)

    VRBO

    Lake Idylwild Delight: Waterfront Lakehouse, Private Dock, Tiki Bar, Kid's Jungle Gym, Near Legoland

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Welcome to SUNRISE ON LAKE IDYLWILD! This home has something special for everyone in your family. This beautifully dec ...

    From $350 per night (USD)

    VRBO

    Details
  • Lake Lucerne way villa
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    Expedia

    Lake Lucerne way villa

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Villa Lake Lucerne, located just around 30 minutes from the Disney World Resort and 17 minutes from the LEGO- ...

    Click For Pricing

    Expedia

    Details
  • Soak up the charm of this cozy, recently  remodel studio.
    From $99 per night (USD)

    VRBO

    Soak up the charm of this cozy, recently remodel studio.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This studio is located minutes from Downtown Winter Haven, one of Florida's oldest towns. The small downtown is packed ...

    From $99 per night (USD)

    VRBO

    Details
  • Modern HouseBoat*AceLoca*4Miles*LegoLand*
    From $132 per night (USD)

    Expedia

    Modern HouseBoat*AceLoca*4Miles*LegoLand*

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to the SeaRover on Lake Mariam part of the Chain of Lakes! This is a fully furnished newly renovated house boat ...

    From $132 per night (USD)

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    Details
  • Fantastic Water Front Home on the Chain of Lakes
    From $468 per night (USD)

    VRBO

    Fantastic Water Front Home on the Chain of Lakes

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitche ...

    From $468 per night (USD)

    VRBO

    Details
  • Confidently Clean, Quint & Cozy Apartment
    From $114 per night (USD)

    Expedia

    Confidently Clean, Quint & Cozy Apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    This is a unique 2 story antique building that has been completely renovated into 4 small apartments. This property was ...

    From $114 per night (USD)

    Expedia

    Details
  • Lake life living 45 mins from most central FL theme parks...
    From $308 per night (USD)

    VRBO

    Lake life living 45 mins from most central FL theme parks...

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Older home very spacious 3 bedrooms, 3 baths large back porch looking over the pool as well as Lake Shipp also on the c ...

    From $308 per night (USD)

    VRBO

    Details
  • Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
    From $579 per night (USD)

    Expedia

    Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    11

    Ready for some Lake with a New Dock & Lego fun - Lake Silver Retreat in the Heart of the City will take your breath away ...

    From $579 per night (USD)

    Expedia

    Details
  • Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure\n
    From $262 per night (USD)

    VRBO

    Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure\n

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Enjoy your stay in this Historic, large, peaceful, fully renovated Plantation home. This home consists of 5 bedrooms, 3 ...

    From $262 per night (USD)

    VRBO

    Details
  • Winter Haven Apt: 1 Mi to Polk State College!
    From $112 per night (USD)

    Expedia

    Winter Haven Apt: 1 Mi to Polk State College!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Close to Polk State College, this convenient, vibrant vacation rental is great for prospective students and alumni, visi ...

    From $112 per night (USD)

    Expedia

    Details
  • Studio Apartment in Winter Haven, FL
    From $130 per night (USD)

    VRBO

    Studio Apartment in Winter Haven, FL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to our studio apartment, a perfect retreat for solo travelers or couples seeking a comfortable and convenient pl ...

    From $130 per night (USD)

    VRBO

    Details
  • Peaceful Lakeside Retreat
    From $377 per night (USD)

    Expedia

    Peaceful Lakeside Retreat

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Tranquility awaits you at this beautiful lakefront home. We invite you to enjoy the best of Florida indoor/outdoor livi ...

    From $377 per night (USD)

    Expedia

    Details
  • Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!
    From $206 per night (USD)

    VRBO

    Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the best sunset in Winter Haven on a hammock, then drive 3 mins for dinner downtown. You can't beat this slice of ...

    From $206 per night (USD)

    VRBO

    Details
  • Comfortable bedroom and house to stay in w\/ swimming pool.
    From $144 per night (USD)

    Expedia

    Comfortable bedroom and house to stay in w\/ swimming pool.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The bedroom i am renting is very comfortable, has tv, dresser, bistro table and chairs, floor lamp, two night stands wit ...

    From $144 per night (USD)

    Expedia

    Details
  • Carefree Cove on Lake Connie - With Hot Tub! 15 mins to Legoland
    From $265 per night (USD)

    VRBO

    Carefree Cove on Lake Connie - With Hot Tub! 15 mins to Legoland

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled on the shores of Winter Haven's Lake Connie, this charming 3-bedroom promises a tranquil escape. This cozy lake ...

    From $265 per night (USD)

    VRBO

    Details
  • 3br\/2ba Haven away from home w\/master suite, 6 mi. to Legoland & pet-friendly!
    From $181 per night (USD)

    Expedia

    3br\/2ba Haven away from home w\/master suite, 6 mi. to Legoland & pet-friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Location, Location, Location ! Bring the whole family to this spacious home with lots of room for fun! Centrally locate ...

    From $181 per night (USD)

    Expedia

    Details
  • 341 Legoland Sherman's Antiques Lake Silver
    From $335 per night (USD)

    VRBO

    341 Legoland Sherman's Antiques Lake Silver

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Summary: Welcome to our charming home located in a peaceful neighborhood, perfect for families and small groups. This co ...

    From $335 per night (USD)

    VRBO

    Details
  • Lake House on the LEGOLAND Chain-of-Lakes with private beach and boat dock
    From $292 per night (USD)

    Expedia

    Lake House on the LEGOLAND Chain-of-Lakes with private beach and boat dock

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Stay comfortably in Central Florida at this 4-bedroom Lakefront Home on the Lego Land Chain-of-Lakes! With two Master Su ...

    From $292 per night (USD)

    Expedia

    Details
  • Family-Friendly Haven near Downtown - Fast Wifi
    From $158 per night (USD)

    VRBO

    Family-Friendly Haven near Downtown - Fast Wifi

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Escape to our inviting 3-bedroom, 1-bath Family-Friendly Retreat near downtown Winter Haven, FL—a haven for fam ...

    From $158 per night (USD)

    VRBO

    Details
  • Cozy Winter Haven Escape | Pet-Friendly\/Fenced Lot
    From $164 per night (USD)

    Expedia

    Cozy Winter Haven Escape | Pet-Friendly\/Fenced Lot

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Welcome to Cozy Retreat near Legoland! Our charming 3-bedroom, 1-bath home offers a pullout sofa bed, a fully s ...

    From $164 per night (USD)

    Expedia

    Details
  • Tiny Paradise
    From $142 per night (USD)

    VRBO

    Tiny Paradise

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Winter Haven studio boasts 1 inviting bedroom with a full bed. The space is equipped with essentials like WiFi, hea ...

    From $142 per night (USD)

    VRBO

    Details
  • 15 minutes to Legoland- Serene Lakeside Cottage Retreat
    From $324 per night (USD)

    Expedia

    15 minutes to Legoland- Serene Lakeside Cottage Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your serene escape in Winter Haven, just minutes away from the excitement of Legoland! This enchanting 3-bedr ...

    From $324 per night (USD)

    Expedia

    Details
  • Spacious 4-bedroom Corporate Home with AC, WiFi in gorgeous Winter Haven
    From $144 per night (USD)

    VRBO

    Spacious 4-bedroom Corporate Home with AC, WiFi in gorgeous Winter Haven

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Make yourself at home in this 4-bedroom Winter Haven retreat. This corporate, short or mid term rental home boasts beaut ...

    From $144 per night (USD)

    VRBO

    Details
  • 6BR Lakefront Escape w\/ Heated Pool, Game Room, Fire Pit, Dock – Perfect for Family Gatherings & Fun
    From $585 per night (USD)

    Expedia

    6BR Lakefront Escape w\/ Heated Pool, Game Room, Fire Pit, Dock – Perfect for Family Gatherings & Fun

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Escape to Emerald Anchor Escape, a spacious 6-bedroom lakefront retreat in Winter Haven, designed for the ultimate famil ...

    From $585 per night (USD)

    Expedia

    Details
  • *3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
    From $291 per night (USD)

    VRBO

    *3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    WELCOME! Lake Mariam Vacation Home (2) is part of a duplex built in 2016 that sits on 2.6 acres of Lakefront Property. I ...

    From $291 per night (USD)

    VRBO

    Details
  • *3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722
    From $164 per night (USD)

    Expedia

    *3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    WELCOME! Lake Mariam Vacation Home (1), is part of a duplex that sits on 2.6 acres of Lakefront Property. There is also ...

    From $164 per night (USD)

    Expedia

    Details
  • CELEBRATE!! Sun, Fun, Relax- Suite- 2 Queen Beds
    From $168 per night (USD)

    VRBO

    CELEBRATE!! Sun, Fun, Relax- Suite- 2 Queen Beds

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    You’ll find the basic amenities like a microwave and refrigerator in every room. Our suites include a sofa bed and some ...

    From $168 per night (USD)

    VRBO

    Details
  • Amazing!!! WINTER HAVEN 2 Queen Beds fun 4 All
    From $183 per night (USD)

    VRBO

    Amazing!!! WINTER HAVEN 2 Queen Beds fun 4 All

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Make the most of your time in Winter Haven with our amenities, which allow you to focus on the people and experiences th ...

    From $183 per night (USD)

    VRBO

    Details
  • Winter Haven-Historic property- N Legoland Sleep 4
    From $187 per night (USD)

    VRBO

    Winter Haven-Historic property- N Legoland Sleep 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to the great property. This historic property was the home of The Red Sox spring training for decades and the so ...

    From $187 per night (USD)

    VRBO

    Details
  • Fun and Relaxation in Winter Haven!! 2 Queen Beds,
    From $183 per night (USD)

    VRBO

    Fun and Relaxation in Winter Haven!! 2 Queen Beds,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our pet-friendly guest room offers free light breakfast item together with your choice of coffee, tea and juice to start ...

    From $183 per night (USD)

    VRBO

    Details
  • Charming Town House — 10 Minutes from the Legoland Park and Downtown
    From $134 per night (USD)

    VRBO

    Charming Town House — 10 Minutes from the Legoland Park and Downtown

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This house is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive from the Legol ...

    From $134 per night (USD)

    VRBO

    Details
  • Legoland 3 Bedroom Pet Friendly Pool Home
    From $263 per night (USD)

    Expedia

    Legoland 3 Bedroom Pet Friendly Pool Home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    13

    Bring the whole family to this great place with lots of room for fun. This home is conveniently located only 2.1 miles f ...

    From $263 per night (USD)

    Expedia

    Details
  • Eagle Lake Home < 7 Mi to Legoland!
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    VRBO

    Eagle Lake Home < 7 Mi to Legoland!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    A fun-filled family getaway awaits at this lovely Eagle Lake vacation rental! This 3-bedroom, 2-bathroom home provides e ...

    Click For Pricing

    VRBO

    Details
  • Winter Haven Studio w\/ BBQ Grill: Steps to 2 Lakes
    From $103 per night (USD)

    Expedia

    Winter Haven Studio w\/ BBQ Grill: Steps to 2 Lakes

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience comfort and convenience at this quaint vacation rental in Winter Haven, FL! With quick access to restaurants, ...

    From $103 per night (USD)

    Expedia

    Details
  • 4.4 miles to Legoland. Conveniently located near large highways and interstates.
    From $130 per night (USD)

    VRBO

    4.4 miles to Legoland. Conveniently located near large highways and interstates.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    4.4 miles to Legoland. 36 miles to Disney (43 minutes) Cozy one bed one bath second floor condo. Centrally located. Walk ...

    From $130 per night (USD)

    VRBO

    Details
  • Spacious Modern 4bd\/2ba Home! Amazing Location
    From $321 per night (USD)

    Expedia

    Spacious Modern 4bd\/2ba Home! Amazing Location

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Nestled in the Heart of Winter Haven, the Modern Home offers a remarkable fusion of innovation, convenience, and aesth ...

    From $321 per night (USD)

    Expedia

    Details
  • Serene, Cozy, Lakefront home
    From $246 per night (USD)

    VRBO

    Serene, Cozy, Lakefront home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Cozy meets calm at this quaint lakefront home. We are located on the Chain of Lakes in Winter Haven, where the waterfr ...

    From $246 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom condo in delightful Winter Haven with AC, WiFi
    From $180 per night (USD)

    Expedia

    Cozy 1-bedroom condo in delightful Winter Haven with AC, WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Winter Haven, this welcoming condo features 1 bedroom with a tremendous king bed. Guests can enjoy the jetted ...

    From $180 per night (USD)

    Expedia

    Details
  • Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
    From $332 per night (USD)

    VRBO

    Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a relaxing stay in this spacious and comfortable home, perfect for families or groups. The open layout of the livi ...

    From $332 per night (USD)

    VRBO

    Details
  • Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
    From $315 per night (USD)

    Expedia

    Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 gue ...

    From $315 per night (USD)

    Expedia

    Details
  • The Unique cozy studio
    From $95 per night (USD)

    VRBO

    The Unique cozy studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Super comfortable! Modern clean fully functioning. centrally located in Winter Haven. 1/2 mile to downtown, less than 4 ...

    From $95 per night (USD)

    VRBO

    Details
  • Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
    From $164 per night (USD)

    Expedia

    Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This cozy bungalow includes 3 bedrooms and 1 ½ baths, and it sleeps up to 8 guests comfortably! Located approximately ...

    From $164 per night (USD)

    Expedia

    Details
  • The Old Haven - An Enduring Piece of Nostalgia
    From $314 per night (USD)

    VRBO

    The Old Haven - An Enduring Piece of Nostalgia

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfe ...

    From $314 per night (USD)

    VRBO

    Details
  • Spacious 5-bedroom house with WiFi, AC in welcoming Winter Haven
    From $487 per night (USD)

    Expedia

    Spacious 5-bedroom house with WiFi, AC in welcoming Winter Haven

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    The Winter Haven home features five welcoming bedrooms, complete with two double beds and five single beds. It also incl ...

    From $487 per night (USD)

    Expedia

    Details
  • Cozy 1-Bedroom Retreat Near Downtown & Legoland
    From $146 per night (USD)

    VRBO

    Cozy 1-Bedroom Retreat Near Downtown & Legoland

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your perfect getaway! This charming one-bedroom unit offers all the essentials for a comfortable stay. The un ...

    From $146 per night (USD)

    VRBO

    Details
  • The Lakeview Oasis Getaway!
    From $700 per night (USD)

    Expedia

    The Lakeview Oasis Getaway!

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    21

    Bring your family & friends and enjoy this amazing & relaxing lakefront view property with room for everyone to come tog ...

    From $700 per night (USD)

    Expedia

    Details
  • An Amazing Mid-Century Modern Experience
    From $512 per night (USD)

    VRBO

    An Amazing Mid-Century Modern Experience

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Welcome to The Gene Leedy House, the life-long residence of iconic architect, Gene Leedy. A founding member of the Saras ...

    From $512 per night (USD)

    VRBO

    Details
  • Waterfront Vacation Rental on Lake Mirror!
    From $110 per night (USD)

    Expedia

    Waterfront Vacation Rental on Lake Mirror!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Situated directly on Lake Mirror, this charming Winter Haven vacation rental is perfect for snowbirds looking to embrace ...

    From $110 per night (USD)

    Expedia

    Details
  • Newly remodeled Vacation Home with Saltwater Pool
    From $250 per night (USD)

    VRBO

    Newly remodeled Vacation Home with Saltwater Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This "brand-new" home, built in 2010, totally rebuilt and remodeled in 2022, is located in a gated community in the sout ...

    From $250 per night (USD)

    VRBO

    Details
  • Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
    From $124 per night (USD)

    Expedia

    Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This private studio room is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive ...

    From $124 per night (USD)

    Expedia

    Details
  • Great Family Home Near Legoland
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    VRBO

    Great Family Home Near Legoland

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    About this space Your family will be close to everything when you stay at this centrally-located home near Legoland and ...

    Click For Pricing

    VRBO

    Details
  • Cozy Family Home Near Legoland
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    Expedia

    Cozy Family Home Near Legoland

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    About this space Relax with the fam after a fun day at LEGOLAND (4.7 miles) or Disney World (36 miles) in our newly reno ...

    Click For Pricing

    Expedia

    Details
  • *CentralLocated*PrivateKingSuitew\/Bath, Washer&Dryer(Eagle)
    From $121 per night (USD)

    VRBO

    *CentralLocated*PrivateKingSuitew\/Bath, Washer&Dryer(Eagle)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); ...

    From $121 per night (USD)

    VRBO

    Details
  • Dock & Lanai: Elegant Villa in Winter Haven!
    From $624 per night (USD)

    Expedia

    Dock & Lanai: Elegant Villa in Winter Haven!

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    8

    WFH Friendly | Lake Access On-Site | 5,100 Sq Ft Escape to the ‘Water Ski Capital of the World’ at this Winter Haven va ...

    From $624 per night (USD)

    Expedia

    Details
  • Winter Haven Abode Near Lakes & Attractions
    From $171 per night (USD)

    VRBO

    Winter Haven Abode Near Lakes & Attractions

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Enjoy a relaxing escape to Winter Haven when you book this charming vacation rental home, complete with 2 bedrooms, 1.5 ...

    From $171 per night (USD)

    VRBO

    Details
  • Lakefront Home w\/ Screened Porch & Grill
    From $237 per night (USD)

    Expedia

    Lakefront Home w\/ Screened Porch & Grill

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Living up to its city name, this elegant 3-bedroom, 3-bathroom Winter Haven home features the perfect haven for a relaxi ...

    From $237 per night (USD)

    Expedia

    Details
  • Lakefront house for rent
    From $196 per night (USD)

    VRBO

    Lakefront house for rent

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    4

    Million dollar lake view. Eagles nest in the back yard every year. No pets. No smoking. No children. No parties. Furnish ...

    From $196 per night (USD)

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    Details
  • PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida
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    PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This room is located 5 minutes from Winter Haven Hospital and is only designed to accommodate women, especially nurses a ...

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  • Peace & Love Room 5 minutes from Winter Haven Hospital
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    Peace & Love Room 5 minutes from Winter Haven Hospital

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Peace & Love Sanitized Private Room with private door entrance and bathroom. Wi-Fi, parking space for a Single person. V ...

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  • TRAVELLING PROFESSIONALS ONLY   - 3.3 miles to Winter Haven Hospital!
    From $98 per night (USD)

    Expedia

    TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    1

    This home is your home away from home. Quiet, clean, full paint job, all new furnishings, Roku TV in both bedrooms, Quee ...

    From $98 per night (USD)

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    Details
  • Lakeside Cottage in Lake Howard (Winter Haven Chain of Lakes)
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    Lakeside Cottage in Lake Howard (Winter Haven Chain of Lakes)

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The Lakeside Cottage sits on Lake Howard, one of the most popular locations on "The Chain of Lakes" near downtown Winter ...

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  • Luxury Home w\/ Lanai, Billiards, 6min to Legoland
    From $462 per night (USD)

    Expedia

    Luxury Home w\/ Lanai, Billiards, 6min to Legoland

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    12

    CHECKOUT A FULL VIDEO OF THE PROPERTY: https://youtu.be/K6zlvwkvq-o ★ SPACIOUS 5-STAR LUXURY WINTER HAVEN HOME ★ You ...

    From $462 per night (USD)

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  • Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
    From $96 per night (USD)

    VRBO

    Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The guesthouse Cute & Cozy is separate yet, it is adjacent to the main house (owner lives) and has its own entrance. L ...

    From $96 per night (USD)

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    Details
  • Beautiful 2bedroom near LEGoLAND
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    Beautiful 2bedroom near LEGoLAND

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Forget your worries in this spacious and serene space. This home is in a nice peaceful neighborhood near winter haven h ...

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  • Luxury StayComfy at WinterHeaven
    From $130 per night (USD)

    VRBO

    Luxury StayComfy at WinterHeaven

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' wi ...

    From $130 per night (USD)

    VRBO

    Details
  • Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks
    From $184 per night (USD)

    Expedia

    Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Nestled along the tranquil shores of Lake Howard, this cozy studio apartment retreat offers breathtaking water views, mo ...

    From $184 per night (USD)

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    Details
  • Vrbo Property
    From $144 per night (USD)

    VRBO

    Vrbo Property

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, ...

    From $144 per night (USD)

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    Details
  • Summer Specials! Pet Friendly, 7 Beds, Family Oasis
    From $453 per night (USD)

    Expedia

    Summer Specials! Pet Friendly, 7 Beds, Family Oasis

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Nestled on the west side of Lake Howard in Winter Haven, the Chain of Lakes Villa offers an enchanting retreat that cele ...

    From $453 per night (USD)

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    Details
  • Winter Haven Home w\/ Pool Near Legoland!
    From $282 per night (USD)

    VRBO

    Winter Haven Home w\/ Pool Near Legoland!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Discover your next family getaway at 'Little Haven!' The modern 3-bedroom, 2-bathroom property provides a comfortable oa ...

    From $282 per night (USD)

    VRBO

    Details
  • Lakefront Winter Haven Retreat: Hot Tub & Patio!
    From $531 per night (USD)

    Expedia

    Lakefront Winter Haven Retreat: Hot Tub & Patio!

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    22

    Located just steps away from the pristine waters of the Chain of Lakes, this stunning 4-bedroom, 3.5-bathroom vacation r ...

    From $531 per night (USD)

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    Details
  • Lakefront condo\n55+ community
    From $170 per night (USD)

    VRBO

    Lakefront condo\n55+ community

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Fully furnished. Bring only your clothing. Pool, shuffle board and dock for fishing. Sunroom included. Covered parking. ...

    From $170 per night (USD)

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    Details
  • Lakefront 2 story 4\/2 bungalo with huge yard.
    From $228 per night (USD)

    Expedia

    Lakefront 2 story 4\/2 bungalo with huge yard.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Property Description fully renovated lake front property with big back porch and yard flowing to the lake. The house has ...

    From $228 per night (USD)

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    Details
  • Winter Haven Vacation Rental ~ 1 Mi to Downtown!
    From $93 per night (USD)

    VRBO

    Winter Haven Vacation Rental ~ 1 Mi to Downtown!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Encompassed by downtown attractions, sprawling lakes, and world-class theme parks, this 1-bed, 1-bath vacation rental in ...

    From $93 per night (USD)

    VRBO

    Details
  • Our Camp at Lake Cannon
    From $364 per night (USD)

    Expedia

    Our Camp at Lake Cannon

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Unbeatable Sunsets - relax @ the lake. Sleeps a Crowd Comfortably We pack in a lot of sleep space. Bunk room includes t ...

    From $364 per night (USD)

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    Details
  • Quiet and cozy 55 plus community .
    From $114 per night (USD)

    VRBO

    Quiet and cozy 55 plus community .

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    2

    Great home in a 55 plus community setting. There are many areas of the home to enjoy. Sitting in the carport, soaking in ...

    From $114 per night (USD)

    VRBO

    Details
  • 4 Bedrm Central Home w\/Gameroom\n\n
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    4 Bedrm Central Home w\/Gameroom\n\n

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    15

    Welcome to this charming house in Winter Haven. This superb property boasts 4 queen beds spread across 4 cozy bedrooms, ...

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  • 4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom\n\n
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    VRBO

    4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom\n\n

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    15

    This enjoyable house in Winter Haven offers 4 cozy bedrooms with a mix of queen, full, twin, and bunk beds. With WiFi, a ...

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    Details
  • Charming 2-bedroom country house with AC, WiFi in Winter Haven
    From $128 per night (USD)

    Expedia

    Charming 2-bedroom country house with AC, WiFi in Winter Haven

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Escape to this marvelous 2-bedroom Winter Haven country house retreat. With a cozy full bed and a comfy twin bed, guests ...

    From $128 per night (USD)

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  • Cozy 3 bedroom central hideaway
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    Cozy 3 bedroom central hideaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy quick and easy self check in with lock box system. Beautiful, quiet and secure community. Enjoy spacious and elega ...

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  •  - HIDDEN GEM - Spacious, minimal and clean! Legoland + Disney
    From $259 per night (USD)

    Expedia

    - HIDDEN GEM - Spacious, minimal and clean! Legoland + Disney

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Consider this house your home away from home while you visit Florida! This fantastic property boasts 4 bedrooms, inclu ...

    From $259 per night (USD)

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    Details
  • Cozy 1-bedroom mobile home with WiFi, AC in enjoyable Winter Haven
    From $71 per night (USD)

    VRBO

    Cozy 1-bedroom mobile home with WiFi, AC in enjoyable Winter Haven

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to this delightful mobile home in picturesque Winter Haven. This cozy retreat offers a bedroom, WiFi, and AC for ...

    From $71 per night (USD)

    VRBO

    Details
  • Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
    From $547 per night (USD)

    VRBO

    Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    11

    Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor ga ...

    From $547 per night (USD)

    VRBO

    Details
  • Large 3\/1 Near DownTown and Dining
    From $257 per night (USD)

    VRBO

    Large 3\/1 Near DownTown and Dining

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to our spacious and modern retreat, perfectly situated in the heart of the city. This stylish home is designed ...

    From $257 per night (USD)

    VRBO

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  • 5 Bedroom Chain of Lakes Home w\/AC Pet Friendly
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    5 Bedroom Chain of Lakes Home w\/AC Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    16

    Bring the wwireless network kitchen for cooking air conditioner television washing machine supporting facilities free pa ...

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    Details
  • Vintage Love Studio
    From $111 per night (USD)

    VRBO

    Vintage Love Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Come and souk up the uniqueness and custom build of this vintage place, turned into a luxurious oasis. This is a cozy st ...

    From $111 per night (USD)

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    Details
  • Lake Shipp House with pool and dock on the water
    From $281 per night (USD)

    VRBO

    Lake Shipp House with pool and dock on the water

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Fully furnished single story home on Lake Shipp; has boat dock, inground heated swimming pool. Two bedrooms (king & quee ...

    From $281 per night (USD)

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    Details
  • Updated 2 Bedroom Condo On Lake Lulu
    From $116 per night (USD)

    VRBO

    Updated 2 Bedroom Condo On Lake Lulu

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Conveniently locate in Winter Haven one mile from Lego Land and Shopping. Two bed rooms, updated kitchen, balcony, commo ...

    From $116 per night (USD)

    VRBO

    Details
  • Spacious 3 Bed, 2 Bath Home Near Legoland
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    Spacious 3 Bed, 2 Bath Home Near Legoland

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    About this space A gem in the Heart of Winter Haven. This brand new 3 bedroom, 2 bathroom home is fresh, clean and ready ...

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  • Cheerful 4 Bed, 3 Bath Home with Screened Pool
    From $317 per night (USD)

    VRBO

    Cheerful 4 Bed, 3 Bath Home with Screened Pool

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    About this space This stylish place to stay is perfect for vacation. With 2 ensuite bedrooms plus 2 additional rooms and ...

    From $317 per night (USD)

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    Details
  • Florida Beachy Palms 2\/1 Home. No Cleaning Fee!
    From $132 per night (USD)

    Expedia

    Florida Beachy Palms 2\/1 Home. No Cleaning Fee!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, ce ...

    From $132 per night (USD)

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  • Cheerful New Construction Home
    From $442 per night (USD)

    VRBO

    Cheerful New Construction Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Bring the whole family to this great place with lots of room for fun. Winter Haven is the up and coming city. Boasting b ...

    From $442 per night (USD)

    VRBO

    Details
  • A lakeside sunset delight near Disney, Universal, Sea World, Busch, LegoLand
    From $195 per night (USD)

    Expedia

    A lakeside sunset delight near Disney, Universal, Sea World, Busch, LegoLand

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    We are open after Milton and have full power. Here's the place to kick back, fish and recharge or to enjoy endless attr ...

    From $195 per night (USD)

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    Details
  • Looking for Relaxation?Near Legoland and Disney
    From $202 per night (USD)

    VRBO

    Looking for Relaxation?Near Legoland and Disney

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Newly renovated 3 bedroom, 2 bathroom house located in a quiet neighborhood in Lake Alfred, Florida. House has own priva ...

    From $202 per night (USD)

    VRBO

    Details
  • Experience family fun! LEGOLAND® Florida just a 12-min drive
    From $316 per night (USD)

    Expedia

    Experience family fun! LEGOLAND® Florida just a 12-min drive

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    In this cozy town of Winter Haven, you'll find a beautiful 4-bedroom house that's just a short 12-minute ride away from ...

    From $316 per night (USD)

    Expedia

    Details
  • View Container 5*Centrally Located*Private Bed\/Bath
    From $99 per night (USD)

    VRBO

    View Container 5*Centrally Located*Private Bed\/Bath

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    WELCOME! Lake Mariam Container Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, ou ...

    From $99 per night (USD)

    VRBO

    Details
  • Waterfront Winter Haven Home with Dock & Hot Tub!
    From $573 per night (USD)

    Expedia

    Waterfront Winter Haven Home with Dock & Hot Tub!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental, perfect for your 'Sunshine State' ...

    From $573 per night (USD)

    Expedia

    Details